Apartments in Province of Siena and Villas – Holiday Lettings - Holiday Rentals Province of Siena

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6,069 Holiday homes

(5) Very Good 

20

Montalcino self-catering farmhouse from £112/night. Child friendly with bbq / golf within 30mins drive

Province of Siena / Montalcino

7 14 1 night min

  • 7 bedrooms
  • sleeps 14
  • 1 night min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

from £113 / night

£786 / week

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from £113 / night

(15) Excellent 

10

Holiday townhouse in Sovicille, Province of Siena, from £99/night. With garden, balcony / terrace and much more!

Province of Siena / Sovicille

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

from £99 / night

£691 / week

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Responds fast!
avg. 3 hours 40 minutes

from £99 / night

(3) Excellent 

18

Castelnuovo dell'Abate house great for fishing, staffed property from £99/night

Montalcino / Castelnuovo dell'Abate

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 50 km
  • Child friendly

from £99 / night

£691 / week

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from £99 / night

(8) Very Good 

20

Holiday rental in Monticiano with bbq, garden

Province of Siena / Monticiano

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from £72 / night

£503 / week

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from £72 / night

(16) Excellent 

36

Unique cottage in Gracciano, Montepulciano | Sleeps 6, pet friendly, swimming pool

Montepulciano / Gracciano

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Lovely Place in the Heart of Tuscan Countryside” Il Saraco is a lovely property situated approximately 1.5 miles from the village of Gracciano, Montepulciano. It is a beautifully restored barn with far reaching views amidst acres of vines. Our host, Laura, is very friendly and accommodating. The apartment is well furnished and spotlessly clean with a well equipped kitchen, large living area, good sized bathroom and two double bedrooms, which are air conditioned (if required). there are stone floors throughout. All windows are fitted with the bug blinds and shutters. We simply closed all the shutters during the heat of the day, then opened all of the windows and the air flowed through during the night, keeping the place comfortably cool. The towels and linens are of good quality and our bed was very comfortable. There if a lovely private shaded patio and large mature garden with plenty of natural shade and a swimming pool. Free, reliable and fast wifi is available to stay in touch with the outside world. Nearby there a several very good, reasonably priced, restaurants. The location is great to exploring Tuscany and you catch a high speed train to places such as Rome from Chuisi. We will definitely visit again in the future.

from £90 / night

£503 - £1,848 / week

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from £90 / night

(5) Excellent 

29

Self-catering holiday rental in Radicofani, Province of Siena | swimming pool and garden - pet friendly property

Province of Siena / Radicofani

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £144 / night

£611 - £961 / week

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from £144 / night

(5) Excellent 

21

Stay at this villa in Casaglia with solarium / roof terrace, swimming pool & bbq from £135/night

San Gimignano / Casaglia

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

from £135 / night

£899 - £2,156 / week

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Responds fast!
avg. 1 hour 6 minutes

from £135 / night

(4) Excellent 

20

Townhouse in Siena with garden - from £81/night

Province of Siena / Siena

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Private garden

from £81 / night

£431 / week

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from £81 / night

25

Excellent value-for-money apartment in Castellina In Chianti from £49/night | walking holidays & pet friendly

Province of Siena / Castellina In Chianti

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Nearest beach 90 km
  • Child friendly
  • Private garden

from £50 / night

£346 / week

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from £50 / night

(1) Very Good 

16

Contignano - apartment with a very good review rating | fireplace & wi-fi | city breaks

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly

from £72 / night

£359 / week

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from £72 / night

11

Looking for child friendly accommodation in Radicofani? Rent this apartment from £65/night

Province of Siena / Radicofani

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £65 / night

£452 / week

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Responds fast!
avg. 3 hours 33 minutes

from £65 / night

(4) Excellent 

36

Villa in Cetona with balcony / terrace | cycling holidays, tennis in town & horse riding | From £153/night

Province of Siena / Cetona

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Private garden

from £153 / night

£1,030 - £1,549 / week

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from £153 / night

12

Pet friendly rental - 1 bedroom in Radicofani, Province of Siena with mountain views

Province of Siena / Radicofani

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £65 / night

£452 / week

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Responds fast!
avg. 3 hours 33 minutes

from £65 / night

(11) Excellent 

34

Pet friendly accommodation in Montepulciano with bbq, sleeps 4, cycling holidays

Province of Siena / Montepulciano

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Air conditioning

from £81 / night

£538 - £691 / week

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from £81 / night

12

Ideal apartment in Chianciano Terme from £72/night | 1 bedroom, sleeps 4

Province of Siena / Chianciano Terme

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £72 / night

£503 / week

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from £72 / night

(6) Excellent 

17

Fantastic rental in Cetona, Province of Siena - Great for walking holidays and horse riding | garden

Province of Siena / Cetona

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Ask owner if suitable for children
  • Ask about pets

from £50 / night

£350 / week

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from £50 / night

(5) Excellent 

19

Holiday rental in Montepulciano from £103/night. Sleeps 4, 2 bedrooms

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly

from £104 / night

£619 - £902 / week

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from £104 / night

(5) Excellent 

16

Top rated holiday apartment in Radda in Chianti | pet friendly | Sleeps 3 | walking holidays

Province of Siena / Radda in Chianti

1 3 4 nights min

  • 1 bedroom
  • sleeps 3
  • 4 nights min
  • Child friendly
  • Ask about pets

from £50 / night

£350 / week

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from £50 / night

(52) Excellent 

19

Amazing apartment in San Gimignano from £175/night | balcony / terrace, air conditioning & garden

Province of Siena / San Gimignano

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
“A modern Tuscan beauty - FANTASTIC accommodation” Azzurra is as beautiful as the name suggests. The photos on line are accurate as the villa is modern, extremely well equipped, furnished and decorated. Beds are comfortable, both showers and bathrooms modern and complete. All appliances are new and easy to use. Our week was over too quickly as none of us wanted to leave and all of us (we were two couples) rushed back to Azzurra in the evening to make supper in the gourmet kitchen and share wine on the private patio and watch the sun set. There are two private seating areas at the villa joined by a third giving a panoramic view. The gardens surrounding the villa were in full bloom in late June and made the accommodation both pleasing to the eye and private. The owner has thought of every possible need you could have, you don't need to bring anything except your groceries and wine...and you will want to buy some local wine. A car is a must and the driving instructions provided are detailed and simple to follow. It is an easy drive to San Gimignano, Volterra (20 minutes) as well as Sienna, Pisa, Lucca, Livorno, Florence or Montepuliciano (Florence being the furthest at a little over an hour). The villa on a private Tuscan hilltop even has WiFi but who wants to spend time on an iPad when the views are so breathtaking!

from £176 / night

£916 - £1,450 / week

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Responds fast!
avg. 2 hours 1 minutes

from £176 / night

4

Holiday hotel apartment with 2 bedrooms and garden in Celle sul Rigo

San Casciano dei Bagni / Celle sul Rigo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool

from £65 / night

£449 / week

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from £65 / night

(6) Very Good 

56

Holiday accommodation in Montefollonico with great reviews | solarium / roof terrace, garden | horse riding

Torrita di Siena / Montefollonico

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £171 / night

£1,195 / week

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from £171 / night

(9) Excellent 

24

Farmhouse in Sarteano from £144/night | 2 bedrooms, sleeps 5

Province of Siena / Sarteano

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £144 / night

£988 / week

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from £144 / night

(4) Excellent 

17

Self-catering house in Cetona with balcony / terrace & fireplace - Great for walking holidays

Province of Siena / Cetona

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min

from £63 / night

£440 / week

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from £63 / night

(1) Excellent 

16

Farmhouse in Radicofani with garden from £108/night - Perfect for walking holidays, golf within 30mins drive & cycling holidays

Province of Siena / Radicofani

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £108 / night

£538 - £763 / week

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from £108 / night

23

Child friendly house in Campiglia d'Orcia, Province of Siena - 3 bedrooms | wi-fi

Province of Siena / Campiglia d'Orcia

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly

from £81 / night

£449 - £1,014 / week

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from £81 / night

(19) Very Good 

Certificate of Excellence

19

Villa in San Gimignano that has earned great reviews from travellers from £79/night - Perfect for walking holidays

Province of Siena / San Gimignano

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £79 / night

£550 - £950 / week

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Responds fast!
avg. 3 hours 57 minutes

from £79 / night

(1) Very Good 

32

Enjoy fishing and city breaks in Castellina In Chianti at this apartment from £62/night

Province of Siena / Castellina In Chianti

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £62 / night

£440 - £1,293 / week

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from £62 / night

(6) Excellent 

68

2 bedroom farmhouse in Radda in Chianti from £72/night | balcony / terrace & wi-fi

Province of Siena / Radda in Chianti

2 3 5 nights min

  • 2 bedrooms
  • sleeps 3
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly

from £72 / night

£449 / week

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from £72 / night

(18) Excellent 

22

Apartment rental in Gaiole in Chianti with garden, wi-fi, cycling holidays from £110/night

Province of Siena / Gaiole in Chianti

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Perfect holiday base for visiting central tuscany” We had a lovely time at Casacorvo Minore - the apartment was perfect - everything you need to enjoy your stay. Easy walking distance to the centre of Gaiole, where there were some lovely restaurants, and a fantastic takeaway pizzeria! Supermarket had everything we need and there were some other lovely little shops to get treats. Wine tasting was within walking distance (involved beautiful walks in the tuscan hills). Only downside was the weather - would probably not go in november again, as a bit wet and the wine tasting was slowing down!

from £110 / night

£560 - £760 / week

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from £110 / night

(1) Excellent 

24

Escape to Sarteano, Province of Siena in this beautiful holiday townhouse | Sleeps 2, 1 bedroom

Province of Siena / Sarteano

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Suitable for children age 5+

from £72 / night

£503 / week

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from £72 / night

(2) Excellent 

7

Experience a home from home at this farmhouse in Montepulciano | wi-fi & garden

Province of Siena / Montepulciano

4 4 2 nights min

  • 4 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £63 / night

£378 / week

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from £63 / night

36

House with swimming pool, wi-fi, garden & more in Rigomagno

Sinalunga / Rigomagno

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £84 / night

£583 - £1,336 / week

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from £84 / night

(1) Excellent 

29

Farmhouse in Montepulciano with balcony / terrace from £126/night - Great for walking holidays

Province of Siena / Montepulciano

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 116 km
  • Child friendly
  • Pet friendly

from £126 / night

£628 / week

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from £126 / night

7

Holiday farmhouse rental

Province of Siena / Sarteano

4 9 3 nights min

  • 4 bedrooms
  • sleeps 9
  • 3 nights min
  • Child friendly

from £207 / night

£1,321 / week

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from £207 / night

24

1 bedroom accommodation in Celle sul Rigo

San Casciano dei Bagni / Celle sul Rigo

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly

from £72 / night

£315 / week

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from £72 / night

(1) Excellent 

18

Comfortable house in Province of Siena. Sleeps 4 in Montepulciano

Province of Siena / Montepulciano

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £95 / night

£661 / week

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from £95 / night

41

Townhouse with 5 bedrooms in Rigomagno, Sinalunga | walking holidays, cycling holidays & city breaks

Sinalunga / Rigomagno

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child friendly

from £72 / night

£503 / week

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from £72 / night

(3) Excellent 

22

Private apartment with 3 bedrooms in Le Piazze | swimming pool, city breaks and more

Province of Siena / Le Piazze

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £63 / night

£449 - £718 / week

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from £63 / night

(5) Excellent 

28

Spacious self catering property in Cetona | sleeps 8 | mountain views, pet friendly, swimming pool

Province of Siena / Cetona

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £126 / night

£807 - £1,794 / week

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from £126 / night

18

Grab a bargain holiday rental in Gaiole in Chianti | Holiday condo from £49/night | Sleeps 5

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £50 / night

£323 / week

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from £50 / night

Top Destination reviews

Stunning farmhouse apartment located between Tuscan cities of San Gimignano and Volterra, shared pool, private garden, sleeps 6
Excellent stay in Tuscany

We enjoyed a great stay at this apartment. It was very comfortable and well equipped - wifi and air conditioning were really good to have and the well kept swimming pool was very welcome in the hot afternoons. The apartment has a beautiful view over the Tuscan hills and is well located - easy drives to local towns, restaurants and wineries plus rail station as/when needed. Mary Ann ensured that everything was in good order and ran smoothly. Recommended.see more
Farmhouse in old mill in the Chianti hills
A fantastic Tuscany retreat

We spent 2 weeks in the guest residence and found the location ideal to visit all of the wonders Tuscany has to offer with even a train station that will take you to Siena in 15 minutes within walking distance if you prefer not to drive. Monteriggioni is a short walk away along footpaths and the whole area is beautiful. The property had everything we as a family of 4 needed plus the added Tuscany charm of a traditional building. My children used the pool every day we were there and we couldn't fault the pool area and gardens for appearance and facilities. The owners are very friendly, available when you need them and can offer a lot of help with deciding where to go or on practical matters such as which supermarket to go to. We were also helped out by the owners with a wine tour booking while we were there which we enjoyed thoroughly. We left with a lot of fond memories of our stay and a camera full of beautiful photographs.see more
Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool
Great Location in heart of Tuscany

We had a lovely stay in Case Felice. Well equipped apartment with fantastic views. The Borgo complex was perfect, we enjoyed a swim most days. The village is about 5 mins walk away with plenty of restaurants and a local co-op. We visited Florence (park on outskirts and got the tram in), Siena (our favourite), Pisa, Monteriggioni, San Gimignano (gets very busy, go early or later in afternoon), Radda and Panzano (recommend MacDarios for an excellent burger!)see more
SIENA,villa,pool,tennis,relax,near Piazza IL CAMPO
Ms

A wonderful villa set on top of a hill with very kind and attentive hosts. They have an eye for detail and a strong goal to deliver a clean fully functioning villa so that you can relax and it works! We spent two weeks here and just got so relaxed that after the first week and the excitement of the Palio, we stopped going to Siena every day and started hanging out at the beautiful pool area. Lazy I know but with such a beautiful view it is hard to resist. Andrea, his wife Elizabetta, and their son Thiago do a great job together. Each has their role. They leave you alone if you are comfortable on your own but if you want something they are there to help in an instant. Their house is the main villa on the property and their front door approachable so you can find them when you need or just say ciao and walk to the pool. It is up to you and they make you feel like you can choose either option depending on your day. They do a really good job as hosts. As for the villa the photos are accurate. I have gone back and checked and what you see in those shots is exactly how it looks. Note the clean modern kitchen and bathrooms. You might not appreciate quite how large the upstairs bedrooms are. They are huge airy and very comfortable with aircon. The downstairs bedroom is best for a child. A flyscreen on the bigger window in this room would help in the hottest part of summer. We would return here and wish the family all the best. Heathersee more
Le Fontanelle - rustic farm buildings with pool
Fab stay in Tuscan hills

We enjoyed a lovely relaxing family holiday at this spacious property in the Tuscan hills. Lots to see and do in the area with plenty of lovely food and good local wines. San Gim is close-by with Florence, Volterra, Pisa, and the Chianti region all easily accessible. … see more
Castello di Montalto - 3 Bedroom Villa in Chianti
Beautiful hideaway

We stayed here for 2 weeks and had an amazing time. Beautiful castle in idyllic setting with really authentic feel. Lovely people in charge who made us feel welcome. Only very minor comments would be that some of the equipment needs an upgrade - bikes weren’t really fit for purpose, lights in bbq area didn’t work, bbq equipment not great Overall a place I would return to.see more